Date: Sat, 12 May 2012 16:05:11 -0400
From: chris_27_ca@yahoo.com
Subject: Michael Chapter 1.  Interracial crossdresser sex

This is a true story about one of my experiences. As usual I changed
people's names for their own privacy. I know it starts out a bit slow, but
just wait and see. XXXOOO Alissa.


It was the late 90's and I was living in the East Bay area of Northern
California in a medium sized city called San Leandro. I was in probably the
best shape of my life, which ironically was due to my lack of money at the
time. Although I had a full time job I didn't make very much per hour so I
was forced to eat quite sensibly and I ran almost everywhere because I
didn't own a car. This wasn't really a problem since my place of employment
was a local gym.

I should start by telling you that I actually did quite good with the
ladies. In fact I had more female bedroom guests than all three of my
roomate's combined, except of course for the one roomate who had a live-in
girlfriend. If you were to see me on the street you see an attractive,
in-shape, heterosexual male. The purpose of this story is to tell you that
looks can be deceiving.

The gym was also an excellent cover story for why I shaved my body on a
daily basis. Many of the other employees and members would shave or wax
their bodies in order to show off the muscular definition they worked so
hard to achieve. As for me I wasn't what you would call heavily muscled,
but I was in pretty good shape. I was moderately tall , (5'11"), and about
180 pounds. I had a nice sleek physique with flat defined abs, nice
muscular legs and a bubble butt from my hours of running. Combine this with
my completely smooth body and you had a recipe for some very kinky
playtime.

I suppose this is as good a time as any to mention that I was also an avid
lifelong crossdresser. I started at a young age trying on my moms clothes
and lingerie. I suppose the fact that she was a biker chick and had plentry
of trashy outfits was quite a bonus in this area. I even used to dabble in
playing with her collection of sex toys, but that is a different story for
another day.

Every so often throughout my life I would get the uncontrollable,
(literally once the idea got in my head it was all encompassing), urge to
dress up in sexy women's clothes for sexual gratification. As I got older
my fantasies when dressed would steer more and more to the idea of getting
fucked by another man. Soon enough it was the only thing I could think
about when I was dressed enfemme. My intent in chronicling this story is to
tell you about one of these events, (one of many), and hopefully provide
you with some sexy reading.

Anyways back to my story. I definitely wasn't what you would call passable,
but when I was done up in full make up, wig and my sluttiest outfit I was
definitely hot. Don't get me wrong, I didn't just look like a guy wearing a
dress either....lol.

 Fortunately for me San Leandro was a lower middle class city with lots of
Hispanic and black citizens. The local women's clothing stores catered to
this demographic by selling lots of tight pants, short skirts, slutty shoes
and skimpy lingerie at a reasonable price.

When I had a little money and the urge overtook me I would wander into
these stores in guy mode and shop for the trashiest outfits I could
find. When I say "urge" it was actually much closer to a compulsion. If any
of you have ever crossdressed then you probably know what I'm talking
about.

My heart raced in my chest and I got an incredible thrill from wandering
through a womans clothing store, looking through the racks of delicious
feminine clothing. I knew it was obvious I was alone and I enjoyed the
stares of the sales girls as I held skimpy outfits up to my torso to judge
if they would fit me.

I would even wander in to PAYLESS shoes and try on the latest women's
shoes. It was an incredible thrill putting on a pair of sexy high heels or
knee high womans boots dressed entirely as a man. My cock would be hard as
a rock and leaking precum as I stood in the aisle wondering if someone was
going to walk around the corner and see me.

Of course the biggest thrill came when I actually brought my purchases up
to the register to pay. The sales girls had mixed reactions. Some would
shake their heads in disgust, some would smile uncomfortably and
some.....would grin knowingly. Either way it made my blood pound in my
veins and my cock harder than spring steel to know that they knew these
slutty clothes were for me.

I would dress as often as I could which was 2-3 times a week as I had
roomates. Once dressed I would cruise the YAHOO chartrooms for local
men. At that time YAHOO allowed user created chartrooms and it was actually
quite easy to find a local chat partner. Most often we would cyber which
always ended with my Cummings into the palm of my hand and coating my
freshly painted fingernails.

Other times I would chat hoping to find a local guy willing to host for
some in-person play time. It was one of these times that I started chatting
with Michael. He was very sweet as we chatted and quite honest about
himself. He told me that he was 30 years old, ( I was 27 at the time), he
was black, and he was on parole for drug sales. Being a white guy who had
never touched more than a little weed as a kid that honestly kind of scared
me.

Michael and I, (Alissa my female name), chatted on-line for about a week
straight. I admitted to him that I was a bit scared to meet up with a black
thug when I would be so obviously vulnerable, (being a boy dressed up in
slutty female clothing), and unable to defend myself if things were to turn
out bad. Michael was very reassuring and genuinely nice. He told me that he
had never been with a guy before but really wanted to meet me after seeing
the pictures that I emailed to him. Michael told me that although he was
straight and did not consider me to be female, he wanted to know what it
was like to feminize a white boy for his pleasure. Little did he know that
that was exactly what I was interested in too.

For many CD's, TV's, TS's it's all about becoming female in the eyes of
their lovers, even if it's just for a short time. For me it was never about
that. I never considered myself to be female, although I did my best to
look and act feminine. For me the thrill was highest when my lover and I
both acknowledged my masculinity, then did our best to destroy it. In other
words I loved being a boy, dressed like a sexy slut who willingly gave up
their manhood to another stronger, more dominant man.

After a week of reassurances and dirty chat with Michael I finally agreed
to meet him. I have to admit the pictures of his large black cock he sent
me had me more than a little excited and nervous.

The day arrived and I thanked my lucky stars for two things, 1) my roomates
weren't home and 2) one of them lent my their car for the day. Going out in
public dressed enfemme was always a special thrill for me. I truly enjoyed
the looks of shock, disgust and sometimes even lust that I received. As I
stated before, I knew I didn't pass 100%, but I did look deliciously
androgynous and I would say my body was very sexy. My goal was never really
to pass for a female, but rather to pass for an attractive guy who was was
wearing womens clothes, a wig and make up and trying to look hot. I looked,
for lack of better words, like a hot crossdresser on the prowl for cock.

I started my transformation the same way as many of my peers, with a nice
long soak in a hot bath. I took my time shaving my body, bring careful not
to leave any stray hairs or knick myself. Once I was done I used some of my
roomate's girlfriends lotions which left me feeling smooth, and smelling
sexy. Next came a liberal amount of deep red nail polish on my toenails and
my mid-length press on nails.

Next I took the time to douche myself. I wasn't sure if things would go
that far, but if they did I was determined to be clean down there for
Michael. I really didn't need to worry because I had barely eaten in the
last 24 hours anyways. I do have to admit that having the douche stem up my
bum felt sexy as he'll though...lol. Once my boy-pussy sparkling clean it
was time to start getting dressed.

Earlier I mentioned my roomate's girlfriend, (I'll call her Allison). She
was a very attractive girl of 23 years old. She worked in women's clothing
retail, (no I never shopped at her store...lol), and always had very sexy
clothes in her closet. I decided that there was a bit of an added thrill
that came from the idea of wearing a real woman's clothing when I stepped
out to meet a male lover. So after some consideration I picked a pair of
skintight low-rise jeans from her closet.

First I slipped into my powder blue Lycra thong panties, taking the time to
tuck my cock back perfectly. It was no small feat because believe it or not
I have a pretty nice package, 7 1/2 inches long, circumcised and
thick. Once I was sufficiently tucked away I slithered into Allison's skin
tight jeans. Lucky for me she had a nice big butt and the jeans were
stretch fit. With a little hopping around my legs and ass were encased in
the dark colored jeans and the waist came to exactly the level of my
hips. I knew that if I bent aggressively at the waist my whale tail would
be showing...yum! I took a look at my ass in the full length mirror and
noticed how big and round it looked. I smiled to myself because i knew it
was exactly the kind of ass a black man would drool over.

Next I put on my matching powder blue Lycra bra and filled the cups with my
c-cup false breast inserts. Once they were adjusted and hanging naturally I
put on my semi-see through long sleeve top. The hem of the shirt came to
just above my navel and was an excellent addition to the low cut jeans. I
completed the outfit with my black knee-high zip up boots with a three inch
stiletto heel, and my black pleather jacket with a hem matching my pink
shirt.

Next I sat down in front of the mirror to apply my make up. Rather than use
my own supplies I decided to take advantage of my roomate's absence and use
Allison's MAC makeup. I took my time, making sure to apply liberal amounts
of eyeliner, eyeshadow, blush and bright red lipstick. Once I was done
putting on my face I put on my shoulder length chestnut real-hair wig and
bobby pinned it in place. The wig cost a small fortune but was worth every
penny because of the realism it added.

I was ready....and I was actually short of breath from excitement, mixed
with fear and adrenaline. Was I really going to do this? This guy could be
dangerous, besides I had never even considered hooking up with a black guy
before. I poured myself a tall glass of white wine to calm my nerves and
took a moment to check myself out while I sipped my vino. What I saw made
my already semi-erect cock strain to free itself from my panties.

I looked amazing! My makeup was flawless. My lips shined with damp desire,
my eyes were dark and mysterious surrounded by the lines of black liner and
dark shaded shadow. As I sat applying it I tried my best to mimic the sexy
style of the Latinas I saw every day at the gym and I was delighted to see
that I nailed it.

My ass and legs looked to die for, Allison's jeans showed the thick
muscularity of my thighs, made my calves taper seductively down into the
top of my black boots while forming a perfect frame for my already plump
ass cheeks. I also noticed that the cut of the jeans made my cock virtually
invisible, leaving a sexy cleft between my thighs right where they met at
my crotch.

I involuntarily grinned at myself in the mirror noting with delight the
natural seductive femininity oozing from my features. Any hesitation I had
been feeling vanished immediately. I grabbed the car keys, threw a tube of
lip stick and a few condoms into my purse and headed out the door, not
caring if any of the neighbors saw me.

As I started the car and put it in gear I could feel my hands shaking and
my head swimming. I was still scared, more scared in fact but the fear made
my desire all the stronger. I loved the feelings I was experiencing as I
drove to our agreed upon meeting place, (a 7-Elleven parking lot), a short
distance away.

I arrived quickly and parked in front of the store to wait for Michael. I
was feeling extremely sexy and confident for some reason so I decided to go
in to the store to buy a drink while I waited. Truthfully I wasn't sure if
Michael would actually show up, (people flaking on you is a big part of
this lifestyle), and I was hoping I might get some inviting looks from some
of the customers. I paid for my drink after making eye contact with a few
guys and walked back out of the store, watching the guys watch me go in a
mirror posted near the door.

As I opened the door to my car I heard a deep baritone voice call out
"Alissa?" from across the parking lot. As I looked in the direction of the
voice I saw an older model Buick with a large muscular black man sitting
behind the steering wheel. He had black dreadlocks that cascaded down to
just above his shoulders and tattoos were visible covering both big
muscular arms. My heart immediately began pounding in my chest! This guy
looked scary and I think I made a really big mistake I thought to myself.